House Sitting Oostburg

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Oostburg, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Patty W.
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Patty W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
50 reviews
15 repeat clients
8 years of experience
Sheboygan, WI, 53081

First time using anyone for staying in-home to sit my cat. Patty was exceptional in the care of my not-so-healthy cat. I had complete confidence in Patty and my cat is doing well upon our return. The “extras” Patty does is above and beyond. I would highly recommend Patty!

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Lori M.
Sitter Profile Image: Hannah & Braxton B.
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Hannah & Braxton B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
18 reviews
2 repeat clients
10 years of experience
Sheboygan, WI, 53081

Thanks for always going above and beyond with my dog! You are the best dog sitter I have had and I will always try to book when available. I love all the updates you give and how in contact you are the whole time. Thank you so much for everything!

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Maggie M.
Sitter Profile Image: Casey V.
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Casey V.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Sheboygan, WI, 53081

About: I have spent years working with dogs, including teaching puppy classes for two years. This gave me a solid foundation in canine behavior and positive reinforcement. Because of my healthcare background, I am exceptionally detail-oriented, reliable, and observant of subtle behavior changes or medical needs. I specialize in dogs of all temperaments—especially anxious, sensitive, or reactive dogs who require a "slow-is-fast" approach. I am calm and safety-focused, prioritizing your dog’s body language and signals over rushed interactions. Whether your dog is high-energy or needs a quiet, structured environment, I provide the consistent care they need to feel safe while you’re away. My schedule is generally flexible, with availability on weekday and weekends. I plan bookings carefully and limit my schedule to ensure each pet recieves attentive, unrushed care. I communicate clearly about timing and am happy to discuss routines and advanced bookings. I follow each owner's instructions carefully and use my experience to create a calm safe environment. I prioritize clear communication, consistancy, and attentive observation to keep pets comfortable and safe.

Sitter Profile Image: Emma B.
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Emma B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Cedarburg, WI, 53012

Emma is amazing! I loved that she wanted to meet me and Lacey before she accepted a job. It was important to her that we were all on the same page. I was able to talk about Laceys needs and routine in person, which really made me feel at ease. When the weekend came for her to stay at our house I was completely comfortable leaving Lacey in her care. She gave me updates and pictures which was great. Thank you Emma!!!!

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Paula R.
Sitter Profile Image: Margaret M.
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Margaret M.
from
$55
per night
5.0 out of 5 stars
2 reviews
1 repeat client
35 years of experience
Bluemound Heights, Milwaukee, WI, 53213

Wow! What can I say? Margaret exceeded every expectation I had for Uecker’s care today! As a new puppy mom who’s only had him for three weeks, leaving him with someone for the first time was a little nerve-wracking. But Margaret made me feel completely at ease. She didn’t just watch him—she played with him, loved on him, reinforced the commands we’ve been working on, and treated him like he was her own. The best part? Walking through the door and finding Uecker snuggled up right next to her. My heart absolutely melted. It was obvious he felt safe, loved, and completely comfortable. I truly couldn’t be happier with the care Margaret provided. Book her before I do, because with my busy schedule, I’ll definitely be calling her again! Thank you so much, Margaret. Uecker already adores you, and so do I!

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Jackie G.
Sitter Profile Image: Jamila M.
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Jamila M.
from
$65
per night
4.9 out of 5 stars
97 reviews
29 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jeremy was great with our dogs and our home. He encouraged play, comforted them, and ensured they were fed and watered appropriately. His intuition to our dogs behavior was also spot on, it’s obvious he is a great care giver. I would highly recommend him!

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Andrea B.
Sitter Profile Image: Jesus K.
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Jesus K.
from
$60
per night
5.0 out of 5 stars
9 reviews
1 repeat client
6 years of experience
Sheboygan, WI, 53081

About: I’ve cared for dogs of all breeds, sizes, and energy levels — from energetic puppies to laid-back seniors. Whether it’s daily walks, feeding, playtime, or administering medications, I treat every dog like they’re my own. I understand how important routine, patience, and positive attention are to your pet’s well-being. I’ve also worked with shy or reactive dogs, and I’m comfortable following any special instructions to make sure your pup feels safe and loved while you’re away. My schedule is currently wide open, so I’m flexible and ready to accommodate your dog’s needs — whether it’s daily walks, last-minute bookings, or ongoing care. I’m available weekdays, weekends, and holidays. Let’s find a time that works best for you and your pup! Your dog’s safety and comfort are my top priorities. I always keep dogs on-leash during walks (unless in a secure, off-leash area with your permission), avoid unsafe routes, and stay alert to other animals or hazards. I closely follow your instructions and routines to keep your pet feeling secure and cared for.

Sitter Profile Image: Leah A.
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Leah A.
from
$60
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
20 years of experience
Fredonia, WI, 53021

Leah was great with my special needs senior, Romeo! We can't wait to have her again!

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Heidi P.
Sitter Profile Image: mia n.
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mia n.
from
$35
per night
19 years of experience
Cascade, WI, 53011

About: i’ve worked with all different size dogs, cats from different age ranges who need medication and lounge, and some others who need training and active walks! i’m currently not working many hours at my job and thought this would be a great way to spend my extra time spending time with animals ! I cuddle and play with my animals! i feed my dog twice a day, and let her outside about 7-8 times a day, unless she walks around with me outside! i give her treats, wash her, clip her toe nails, clean her face, etc.

Sitter Profile Image: Judy & Paul & Melissa P.
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Judy & Paul & Melissa P.
Star Sitter
from
$60
per night
5.0 out of 5 stars
400 reviews
142 repeat clients
20 years of experience
Sheboygan, WI, 53081

Judy could not have possibly been a better sitter. Kind, friendly, and professional. My boy, Axl, absolutely LOVES her. Cannot recommend her enough

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Patrick A.
Sitter Profile Image: Yana C.
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Yana C.
from
$50
per night
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Belgium, WI, 53004

Yana is an amazing sitter. She was very flexible when our schedule changed and communicated very clearly. I can’t say enough good things about our experience! Yana went above and beyond to make sure our dog felt comfortable and cared for.

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Robert R.
Sitter Profile Image: Sofia K.
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Sofia K.
from
$100
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
5 years of experience
Wauwatosa, WI, 53213

Once again, Sofia did a wonderful job taking care of our pup & house & even watering plants! We are so comfortable knowing Sofia is with our precious pup & love the updates & pictures she sends!

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Diane T.
Sitter Profile Image: Taylor D.
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Taylor D.
from
$85
per night
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Sheboygan Falls, WI, 53085

About: Hi! My name is Taylor, I’m a lifelong animal lover with lots of experience caring for both dogs and cats. I work full‑time and am in the office four days a week, with remote work on Fridays, which gives me flexibility at the end of the week and allows me to spend quality time with the pets I’m caring for. I grew up with two golden doodles and a mini pinscher poodle, so I’m comfortable with dogs of all sizes, energy levels, and personalities. I also have experience fostering kittens and caring for multiple pets at once. At home, I have two cats of my own, so I’m very familiar with feline care, routines, and personalities as well. I live in Port Washington and love taking dogs on neighborhood walks or to nearby parks for some fresh air and exercise. Whether your pet needs walks, overnight care, or just some extra company and attention, I’d love to help and make sure they feel safe and comfortable while you’re away! I work full-time remotely, so I’m available for dogsitting during the day! My work will just need to come with me, but your pup will still get plenty of love and attention throughout the day. I make sure your pet feels safe, comfortable, and loved while you're away. Whether at your home or on a walk, I stick to their routine, give plenty of attention, and keep them safe. I’ll also send updates, so you know they’re happy and well cared for!

Sitter Profile Image: Jasmine N.
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Jasmine N.
from
$52
per night
5.0 out of 5 stars
5 reviews
1 repeat client
8 years of experience
Sheboygan Falls, WI, 53085

Jasmine was great- she provided updates & made sure both our dogs were loved on while we were gone. We look forward to having her back!

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Katie K.
Sitter Profile Image: Mya R.
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Mya R.
from
$60
per night
5.0 out of 5 stars
9 reviews
13 years of experience
Sheboygan, WI, 53083

My dog, Jake, loved Mya!!! Will definitely use again when I need a pet sitter.

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Carolyn P.
Sitter Profile Image: Lisa S.
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Lisa S.
from
$70
per night
5.0 out of 5 stars
13 reviews
1 repeat client
25 years of experience
Elkhart Lake, WI, 53020

Lisa was exactly who we were hoping for as a sitter for Buddy. It was our and his first time overnight and she made it very comfortable for all of us. We received some fun photos of Buddy as well. Lisa gave us a full report when we got home. The best news was seeing Buddy going to the door after Lisa left and he was asking us when is she coming back! Highly recommended!

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Pastor Bill T.
Sitter Profile Image: Wendy T.
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Wendy T.
from
$75
per night
15 years of experience
Elkhart Lake, WI, 53020

About: I can't wait to meet you and your furry family member! I've trained my own puppy and attended several dog training classes, giving me a strong understanding of canine behavior and care. I also have experience caring for a senior dog who is blind, which has taught me patience, compassion, and adaptability. My goal is to give your pet exercise, companionship, and attention while taking the stress out of long days at home. I also happily care for cats and treat every pet as if they were my own. 🐕🐈❤️ Need a helping hand with your pet's care? I'm available for 30-minute walks during the lunch hour, as well as weekend walks, check-ins, and pet sitting. I'd love to help keep your pets happy, active, and cared for. I treat every pet with the same love, patience, and attention I give my own. During walks and drop-in visits, I provide exercise, companionship, fresh water, and personalized care based on your pet's unique needs. I carefully follow your instructions regarding feeding schedules, medications, and daily routines to ensure consistency and comfort. For pet sitting, I work to keep your pet's routine as normal as possible while you're away, helping them feel safe, relaxed, and well cared for. I have experience caring for energetic puppies, senior dogs, and pets with special needs, including a blind senior dog. I also care for cats, providing feeding, playtime, litter box maintenance, and plenty of affection. My goal is to give your pets a positive, stress-free experience and give you peace of mind while you're away. 🐾❤️

Sitter Profile Image: Holly E.
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Holly E.
from
$25
per night
5.0 out of 5 stars
2 reviews
3 years of experience
Sheboygan, WI, 53081

Our dogs loved having Holly stay with them while we were away! We got tons of happy photos and daily pup-dates. We highly recommend having Holly care for your animals! :)

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Maggie O.
Sitter Profile Image: Jenn L.
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Jenn L.
from
$50
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
30 years of experience
Mill Valley, Milwaukee, WI, 53224

Jenn was so great with my very spoiled Great Pyrenees at her home Christmas weekend. She was so good at communicating and sending pictures the weekend she was with him. I felt she genuinely cared so much about Koda and us too. I will definitely be contacting her again on our next travels. Thanks again Jenn!

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Michelle P.
Sitter Profile Image: Victoria S.
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Victoria S.
from
$45
per night
20 years of experience
Plymouth, WI, 53073

About: Hello! I am Victoria. I am going to school part-time for Business Management and work full time on 3rd shift, which gives me time during the off hours to drop in and check on your pet as well as take them for a nice walk during the day. I’ve had and taken care of pets since I was 10, mainly dogs, lizards and hamsters. I have experience with dogs ranging from puppies to seniors and am comfortable giving medication as needed. I work 3rd shift. I am available between my sleep schedule, mid day to mid afternoon to care for your pet with drop-ins and take for walks, usually 20-30min. I care for the pet as they were my own. There’s no shortage of walks, scratches, love and cuddles. And any other enrichment the pet may need.

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The median cost per night for house sitting in Oostburg is $50

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Oostburg

Select a filter and find qualifying sitters offering house sitting.

Sitters in Oostburg average 4
repeat house sitting clients

FAQs for House Sitting - Oostburg

Frequently asked questions about Rover

As of August 2026, there are 248 sitters on Rover offering House Sitting across Oostburg. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Oostburg walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Oostburg maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Oostburg choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Oostburg. On Rover:

  • 90% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 100% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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